73986-53-5

Basic information

• Product Name: O-DEMETHLY TRAMADOL
• Synonyms: O-DEMETHLY TRAMADOL;3-[2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenol;O-Desmethyltramadol;Phenol,3-[2-[(diMethylaMino)Methyl]-1-hydroxycyclohexyl]-;3-[2-[(DIMETHYLAMINO)METHYL]-1-HYDROXYCYCLOHEXYL]PHENOL(WXG01631)
• CAS NO: 73986-53-5
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.35
• Mol File: 73986-53-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 403.3 °C at 760 mmHg
• Flash Point: 201.2 °C
• Appearance: /
• Density: 1.104 g/cm³
• Vapor Pressure: 3.14E-07mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: O-DEMETHLY TRAMADOL(CAS DataBase Reference)
• NIST Chemistry Reference: O-DEMETHLY TRAMADOL(73986-53-5)
• EPA Substance Registry System: O-DEMETHLY TRAMADOL(73986-53-5)

Safety Data

• Hazardous Substances Data: 73986-53-5(Hazardous Substances Data)

Usage

Uses

O-Desmethyl Tramadol, is a metabolite of Tramadol, an analgesic.

InChI:InChI=1/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3

Synthetic route

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + O-desmethyltramadol (73986-53-5) → O-desmethyl-tramadol-diclofenac

Conditions	Yield
In isopropyl alcohol at 20℃; Product distribution / selectivity;	100%

O-desmethyltramadol (73986-53-5) + (S)-ibuprofen (51146-56-6) → O-desmethyl-tramadol-(S)-ibuprofen

Conditions	Yield
In toluene at 20℃; for 3h;	91%

3-acetyl-2-hydroxybenzoic acid (67127-78-0) + O-desmethyltramadol (73986-53-5) → O-desmethyl-tramadol-acetylsalicylic acid

Conditions	Yield
In chloroform at 20℃; Product distribution / selectivity;	88%

O-desmethyltramadol (73986-53-5) + triflusal (322-79-2) → O-desmethyl-tramadol-triflusal

Conditions	Yield
In ethyl acetate at 0 - 20℃; for 0.666667h; Product distribution / selectivity; Cooling with ice;	77%

O-desmethyltramadol (73986-53-5) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → O-desmethyl-tramadol-(S)-naproxen

Conditions	Yield
In chloroform Product distribution / selectivity; Heating;	66%

fluorobiprofen (5104-49-4) + O-desmethyltramadol (73986-53-5) → O-desmethyl-tramadol-flurbiprofen

Conditions	Yield
In acetic acid butyl ester Product distribution / selectivity;	65%

N-Boc-gabapentin (227626-60-0) + O-desmethyltramadol (73986-53-5) → (1R2R,1S2S)-3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenyl 2-(1-((tert-butoxycarbonylamino)methyl)cyclohexyl)acetate (1345016-64-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h;	44%

Carbonyldiimidazole (64269-79-0) + ibuprofen (15687-27-1) + O-desmethyltramadol (73986-53-5) → 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl 2-(4-isobutyl-phenyl)-propionate (269079-66-5)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; dichloromethane; water; mineral oil
With sodium hydroxide In tetrahydrofuran; dichloromethane; water; mineral oil

Upstream product

• 2914-77-4 tramadol 
• 36282-47-0 tramadol hydrochloride 
• 27203-92-5 cis-tramadol 

Downstream Products

• 269079-66-5 3-(2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-phenyl 2-(4-isobutyl-phenyl)-propionate 
• 16412-54-7 (+/-)-mono-O-demethyltramadol hydrochloride 
• 1345016-64-9 (1R₂R,1S₂S)-3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenyl 2-(1-((tert-butoxycarbonylamino)methyl)cyclohexyl)acetate 
• 144830-14-8 (+)-O-Demethyltramadol 

Relevant articles and documents

A PROCESS FOR PREPARATION OF O-DESMETHYLTRAMADOL AND SALTS THEREOF

The present invention relates to a process of preparation of O-Desmethyl tramadol through potassium hydroxide mediated demethylation of Tramadol under phase transfer conditions.

COMPOSITIONS AND METHODS FOR OVERCOMING RESISTANCE TO TRAMADOL

There is disclosed a composition for oral administration of O-desmethyltramadol. There is further disclosed a method for treating disorders modulated by at least opiate receptor activity or monoamine activity, including acute and chronic pain, comprising administering a pharmaceutical formulation comprising O-desmethyltramadol. Compositions and methods are also provided that are effective for overcoming resistance to tramadol in patients.